Araştırma Makalesi
BibTex RIS Kaynak Göster
Yıl 2019, Cilt: 7 , 371 - 379, 24.11.2019

Öz

Kaynakça

  • Abraham, J. P., Sajan, D., Hubert, Joe I. H., & Jayakumar, V. S. (2008). Molecular structure, spectroscopic studies and first-order molecular hyperpolarizabilities of p-amino acetanilide, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 71 (2), 355-367. Aggarwal, N., Kumar, R., Dureja, P. & Khurana, J. M. (2011). Synthesis, antimicrobial evaluation and QSAR analysis of novel nalidixic acid based 1,2,4-triazole derivatives, European Journal of Medicinal Chemistry, 46 (9), 4089-4099. Avcı, D. & Atalay, Y. (2008). Theoretical analysis of vibrational spectra and scaling‐factor of 2‐aryl‐1,3,4‐oxadiazole derivatives, International Journal of Quantum Chemistry, 109, 328-341. Bayrak, H., Demirbas, A., Demirbas, N., & Karaoglu, S. A. (2010). Cyclization of some carbothioamide derivatives containing antipyrine and triazole moietieses and investigation of their antimicrobial activities, European Journal of Medicinal Chemistry, 45 (11), 4726-4732. Becke A. D. (1993). Density functional thermochemistry. III. The role of exact Exchange, The Journal of Chemical Physics, 98, 5648-5652. Beytur, M., Turhan Irak, Z., Manap, S., and Yüksek, H. (2019). Synthesis, Characterization and Theoretical Determination of Corrosion Inhibitor Activities of Some New 4,5-Dihydro-1H-1,2,4-Triazol-5-one Derivatives, Heliyon, 5 (6), e01809, 1-8. Çiftçi, E., Beytur, M., Calapoğlu, M., Gürsoy Kol, Ö., Alkan, M., Toğay, V. A., Manap, S., & Yüksek, H. (2018). Synthesis, Characterization, Antioxidant and Antimicrobial Activities and DNA Damage of Some Novel 2-[3-alkyl (aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acids in Human Lymphocytes, Research Journal of Pharmaceutical, Biological and Chemical Sciences, 9 (5), 1760-1771. Crofton KM. 1996. A Structure-Activity Relationship for the Neurotoxicity of Triazole Fungicides. Toxicology Letters (Shannon). 84 (3), 155-159. Dennington, R., Keith, T., & Millam, J. (2009). GaussView, Version 5, Semichem Inc., Shawnee Mission KS. Frisch, A., Nielson, A.B., & Holder, A.J. (2003).Gaussvıew User Manual, Gaussian, Inc., Wallingford, CT, Frisch, M. J., Trucks, G., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Jr. Vreven, T., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, L. R., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J. & Fox, D. J. (2009). Gaussian Inc., Wallingford, CT. Govindarajan, M., Periandy, S., & Carthigayen, K. (2012). FT-IR and FT-Raman spectra, thermo dynamical behavior, HOMO and LUMO, UV, NLO properties, computed frequency estimation analysis and electronic structure calculations on α-bromotoluene. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97, 411-422. Gürsoy Kol, Ö., and Yüksek, H. (2010). Synthesis and invitro antioxidant evaluation of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, E-Journal of Chemistry, 7 (1), 123-136. İkizler, A. A. & Yüksek, H. (1994). Reaction of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones with 2,5-dimetoxytetrahydrofuran, Collection of Czechoslovak Chemical Communications, 59 (3), 731-735. Jamróz, M. H. (2004). Vibrational Energy Distribution Analysis: VEDA 4 program, Warsaw. Karamanis, P, Pouchan, C., & Maroulis, G., (2008). Structure, stability, dipole polarizability and differential polarizability in small gallium arsenide clusters from all-electron ab initio and density-functional-theory calculations, Physical Review A, 77, 013201-013208. Küçükgüzel, Ş. G., & Çıkla Süzgün P. (2015). Recent advances bioactive 1,2,4-triazole-3-thiones, European Journal of Medicinal Chemistry, 97, 830-870. Lee, S. Y. (1998). Molecular Structure and Vibrational Spectra of Biphenyl in the Ground and the lowest Triplet States. Density Functional Theory Study, Bulletin of the Korean Chemical Society, 19 (1), 93-98. Nadeem, H. & Ashraf, Z. (2012). Regiospecific synthesis of some novel N-nucleosides of 4-amino-5- substituted-1,2,4-triazole-3-thiones and their in-vitro antimicrobial activity, European Journal of Chemistry, 3 (4), 485-492. Pir, H., Günay, N., Tamer, Ö., Avcı, D. & Atalay, Y. (2013). Theoretical investigation of 5-(2-Acetoxyethyl)-6-methylpyrimidin-2, 4-dione: Conformational study, NBO and NLO analysis, molecular structure and NMR spectra, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 112, 331-342. Rani, A. U., Sundaraganesan, N., Kurt, M., Çınar, M., & Karabacak, M. (2010). FT-IR, FT-Raman, NMR spectra and DFT calculations on 4-chloro-N-methylaniline, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 75, 1523-1529. Sancak, K., Unver, Y., Kazak, C., Dugdu, E., and Arslan, B. (2010). Synthesis and characterizations of some new 2,4-dihydro-[1,2,4]-triazol-3-one derivatives and X-ray crystal structures of 4-(3-phenylallylideneamino)-5-thiophen-2-yl-methyl-2,4-dihydro-[1,2,4]triazol-3-one, Turkish Journal of Chemistry, 34 (5), 771-780. Subramanian, N., Sundaraganesan, N., & Jayabharathi, J. (2010). Molecular structure, spectroscopic (FT-IR, FT-Raman, NMR, UV) studies and first-order molecular hyperpolarizabilities of 1,2-bis(3-methoxy-4-hydroxybenzylidene)hydrazine by density functional method, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 76, 259-269. Turhan Irak, Z., & Beytur, M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi, Iğdır University Journal of the Institute of Science and Technology, 9 (1), 512-521. Yüksek, H., Üçüncü, O., Alkan, M., Ocak, Z., Bahçeci, Ş., & Özdemir, M. (2005). Synthesis and Determination of pKa Values of Some New 3,4-Disubstituted-4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives in Non-aqueous Solvents, Molecules 10, 961-970. Yüksek, H., Küçük, M., Alkan, M., Bahçeci, S., Kolaylı, S., Ocak, Z., Ocak, U., Şahinbas, E., & Ocak, M. (2006). Synthesis and antioxidant activities of some new 4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their acidic properties, Asian Journal of Chemistry, 18 (1), 539-550. Tereci, H., Askeroğlu, İ., Akdemir, N., Uçar, İ., & Büyükgüngör, O. (2012). Combined experimental and theoretical approaches to the molecular structure of 4-(1-formylnaphthalen-2-yloxy)phthalonitrile, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 96, 569-577. Turhan Irak, Z. & Gümüş, S. (2017). Heterotricyclic compounds via click reaction: A computational study. Noble International Journal of Scientific Research, 1(7), 80-89. Turhan Irak, Z. & Beytur, M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi, Iğdır University Journal of the Institute of Science and Technology, 9 (1), 512-521. Vosko, S. H., Wilk, L. & Nusair, M. (1980). Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, Canadian Journal of Physics. 58, 1200. Wade, Jr. L.G. (2006). Organic Chemistry, 6nd ed.; Pearson Prentice Hall: New Jersey. Wolinski, K., Hinton, J. F. & Pulay, P. (1990). Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. Journal of the American Chemical Society, 112, 8251-8260. Zhang, L.Y., Wang, B.L., Zhan, Y.Z., Zhang, Y., Zhang, X. & Li, Z. M. (2016). Synthesis and biological activities of some fluorine- and piperazine-containing 1,2,4-triazole thione derivatives. Chinese Chemical Letters, 27, 163-167.

Spectroscopic and Nonlinear Optical Properties of Biologically Active 3‐(2/3/4‐Pyridyl)-4‐amino‐1,2,4‐triazole‐5‐thiones by Density Functional Theory Method

Yıl 2019, Cilt: 7 , 371 - 379, 24.11.2019

Öz

In the present study, vibrational frequencies and gauge including atomic orbital (GIAO) 13C-NMR and 1H-NMR chemical shift values of 3‐(2/3/4‐pyridyl)-4‐amino‐1,2,4‐triazole‐5‐thiones in the ground state have been calculated by using the density functional method (B3LYP) with 6-311G(d,p) basis set. The vibrational spectra of the title compounds which is calculated by DFT methods, reproduces vibrational wave numbers and intensities with an accuracy which allows reliable vibrational assignments. The title compounds have been studied theoretically in the 4000–400 cm-1 region and the assignment of all the observed bands were made. In the identification of calculated IR data was used the veda4f program. Theoretical infrared spectrums are formed from the data obtained according to B3LYP method. The calculated IR data of title compounds were calculated in gas phase by using of 6-311G(d,p) basis sets of B3LYP method and are multiplied with appropriate adjustment factors. Also, The 1H- and 13C- nuclear magnetic resonance chemical shifts values of 3‐(2/3/4‐pyridyl)-4‐amino‐1,2,4‐triazole‐5‐thione molecules have been calculated by the gage including atomic orbital (GIAO) method. The calculated 13C-NMR and 1H-NMR chemical shift values compared with the experimental values. Experimental data were obtained from the literature. Furthermore, total static dipol moment (μ), the mean polarizability (<α>), the anisotropy of the polarizability (Δα), the mean first-order hyperpolarizability (<β>), of title compounds have been investigated by using B3LYP levels with the 6-311G(d,p) basis set.

Kaynakça

  • Abraham, J. P., Sajan, D., Hubert, Joe I. H., & Jayakumar, V. S. (2008). Molecular structure, spectroscopic studies and first-order molecular hyperpolarizabilities of p-amino acetanilide, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 71 (2), 355-367. Aggarwal, N., Kumar, R., Dureja, P. & Khurana, J. M. (2011). Synthesis, antimicrobial evaluation and QSAR analysis of novel nalidixic acid based 1,2,4-triazole derivatives, European Journal of Medicinal Chemistry, 46 (9), 4089-4099. Avcı, D. & Atalay, Y. (2008). Theoretical analysis of vibrational spectra and scaling‐factor of 2‐aryl‐1,3,4‐oxadiazole derivatives, International Journal of Quantum Chemistry, 109, 328-341. Bayrak, H., Demirbas, A., Demirbas, N., & Karaoglu, S. A. (2010). Cyclization of some carbothioamide derivatives containing antipyrine and triazole moietieses and investigation of their antimicrobial activities, European Journal of Medicinal Chemistry, 45 (11), 4726-4732. Becke A. D. (1993). Density functional thermochemistry. III. The role of exact Exchange, The Journal of Chemical Physics, 98, 5648-5652. Beytur, M., Turhan Irak, Z., Manap, S., and Yüksek, H. (2019). Synthesis, Characterization and Theoretical Determination of Corrosion Inhibitor Activities of Some New 4,5-Dihydro-1H-1,2,4-Triazol-5-one Derivatives, Heliyon, 5 (6), e01809, 1-8. Çiftçi, E., Beytur, M., Calapoğlu, M., Gürsoy Kol, Ö., Alkan, M., Toğay, V. A., Manap, S., & Yüksek, H. (2018). Synthesis, Characterization, Antioxidant and Antimicrobial Activities and DNA Damage of Some Novel 2-[3-alkyl (aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acids in Human Lymphocytes, Research Journal of Pharmaceutical, Biological and Chemical Sciences, 9 (5), 1760-1771. Crofton KM. 1996. A Structure-Activity Relationship for the Neurotoxicity of Triazole Fungicides. Toxicology Letters (Shannon). 84 (3), 155-159. Dennington, R., Keith, T., & Millam, J. (2009). GaussView, Version 5, Semichem Inc., Shawnee Mission KS. Frisch, A., Nielson, A.B., & Holder, A.J. (2003).Gaussvıew User Manual, Gaussian, Inc., Wallingford, CT, Frisch, M. J., Trucks, G., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Jr. Vreven, T., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, L. R., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J. & Fox, D. J. (2009). Gaussian Inc., Wallingford, CT. Govindarajan, M., Periandy, S., & Carthigayen, K. (2012). FT-IR and FT-Raman spectra, thermo dynamical behavior, HOMO and LUMO, UV, NLO properties, computed frequency estimation analysis and electronic structure calculations on α-bromotoluene. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97, 411-422. Gürsoy Kol, Ö., and Yüksek, H. (2010). Synthesis and invitro antioxidant evaluation of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, E-Journal of Chemistry, 7 (1), 123-136. İkizler, A. A. & Yüksek, H. (1994). Reaction of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones with 2,5-dimetoxytetrahydrofuran, Collection of Czechoslovak Chemical Communications, 59 (3), 731-735. Jamróz, M. H. (2004). Vibrational Energy Distribution Analysis: VEDA 4 program, Warsaw. Karamanis, P, Pouchan, C., & Maroulis, G., (2008). Structure, stability, dipole polarizability and differential polarizability in small gallium arsenide clusters from all-electron ab initio and density-functional-theory calculations, Physical Review A, 77, 013201-013208. Küçükgüzel, Ş. G., & Çıkla Süzgün P. (2015). Recent advances bioactive 1,2,4-triazole-3-thiones, European Journal of Medicinal Chemistry, 97, 830-870. Lee, S. Y. (1998). Molecular Structure and Vibrational Spectra of Biphenyl in the Ground and the lowest Triplet States. Density Functional Theory Study, Bulletin of the Korean Chemical Society, 19 (1), 93-98. Nadeem, H. & Ashraf, Z. (2012). Regiospecific synthesis of some novel N-nucleosides of 4-amino-5- substituted-1,2,4-triazole-3-thiones and their in-vitro antimicrobial activity, European Journal of Chemistry, 3 (4), 485-492. Pir, H., Günay, N., Tamer, Ö., Avcı, D. & Atalay, Y. (2013). Theoretical investigation of 5-(2-Acetoxyethyl)-6-methylpyrimidin-2, 4-dione: Conformational study, NBO and NLO analysis, molecular structure and NMR spectra, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 112, 331-342. Rani, A. U., Sundaraganesan, N., Kurt, M., Çınar, M., & Karabacak, M. (2010). FT-IR, FT-Raman, NMR spectra and DFT calculations on 4-chloro-N-methylaniline, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 75, 1523-1529. Sancak, K., Unver, Y., Kazak, C., Dugdu, E., and Arslan, B. (2010). Synthesis and characterizations of some new 2,4-dihydro-[1,2,4]-triazol-3-one derivatives and X-ray crystal structures of 4-(3-phenylallylideneamino)-5-thiophen-2-yl-methyl-2,4-dihydro-[1,2,4]triazol-3-one, Turkish Journal of Chemistry, 34 (5), 771-780. Subramanian, N., Sundaraganesan, N., & Jayabharathi, J. (2010). Molecular structure, spectroscopic (FT-IR, FT-Raman, NMR, UV) studies and first-order molecular hyperpolarizabilities of 1,2-bis(3-methoxy-4-hydroxybenzylidene)hydrazine by density functional method, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 76, 259-269. Turhan Irak, Z., & Beytur, M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi, Iğdır University Journal of the Institute of Science and Technology, 9 (1), 512-521. Yüksek, H., Üçüncü, O., Alkan, M., Ocak, Z., Bahçeci, Ş., & Özdemir, M. (2005). Synthesis and Determination of pKa Values of Some New 3,4-Disubstituted-4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives in Non-aqueous Solvents, Molecules 10, 961-970. Yüksek, H., Küçük, M., Alkan, M., Bahçeci, S., Kolaylı, S., Ocak, Z., Ocak, U., Şahinbas, E., & Ocak, M. (2006). Synthesis and antioxidant activities of some new 4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their acidic properties, Asian Journal of Chemistry, 18 (1), 539-550. Tereci, H., Askeroğlu, İ., Akdemir, N., Uçar, İ., & Büyükgüngör, O. (2012). Combined experimental and theoretical approaches to the molecular structure of 4-(1-formylnaphthalen-2-yloxy)phthalonitrile, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 96, 569-577. Turhan Irak, Z. & Gümüş, S. (2017). Heterotricyclic compounds via click reaction: A computational study. Noble International Journal of Scientific Research, 1(7), 80-89. Turhan Irak, Z. & Beytur, M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi, Iğdır University Journal of the Institute of Science and Technology, 9 (1), 512-521. Vosko, S. H., Wilk, L. & Nusair, M. (1980). Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, Canadian Journal of Physics. 58, 1200. Wade, Jr. L.G. (2006). Organic Chemistry, 6nd ed.; Pearson Prentice Hall: New Jersey. Wolinski, K., Hinton, J. F. & Pulay, P. (1990). Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. Journal of the American Chemical Society, 112, 8251-8260. Zhang, L.Y., Wang, B.L., Zhan, Y.Z., Zhang, Y., Zhang, X. & Li, Z. M. (2016). Synthesis and biological activities of some fluorine- and piperazine-containing 1,2,4-triazole thione derivatives. Chinese Chemical Letters, 27, 163-167.
Toplam 1 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Zeynep Turhan Irak

Murat Beytur

Yayımlanma Tarihi 24 Kasım 2019
Yayımlandığı Sayı Yıl 2019Cilt: 7

Kaynak Göster

APA Irak, Z. T., & Beytur, M. (2019). Spectroscopic and Nonlinear Optical Properties of Biologically Active 3‐(2/3/4‐Pyridyl)-4‐amino‐1,2,4‐triazole‐5‐thiones by Density Functional Theory Method. The Eurasia Proceedings of Science Technology Engineering and Mathematics, 7, 371-379.